8 Brutal Questions to Ask Before Quitting Your Job to Become an Entrepreneur

I’m going to quit my job.

Right now, my wife and I are teaching english overseas. By the time our contract is over in a few months, that’ll be it. Income generation will come from my business, period.


Below is a list adapted from Robert Kiyosaki’s book Rich Dad’s Before You Quit Your Job: 10 Real-Life Lessons Every Entrepreneur Should Know About Building a Million-Dollar Business (affiliate link). It’s an excellent read, and you should buy it (and not just to give me a 30 cent affiliate bonus, either.)

If you’re thinking of quitting your job to start a business, here are 8 bare bones, straight-to-the-point questions you should ask yourself with brutal frankness.

Keep track of your score for results.

On a Scale of 1–10:

1. What is your desire for freedom instead of security?

2. What is your desire for great wealth instead of a steady paycheck?

3. How much do you value independence instead of dependence?

4. How badly to you want to make your own rules instead of following others’ rules?

5. How willing are you to take full responsibility when things go wrong instead of saying “that’s not my job?”

6. How badly do you want to determine the culture of a company rather than try to fit in some other company’s culture?

7. How badly do you want to make a difference in this world instead of complaining about the world’s problems?

8. How willing are you to turn a problem into a business opportunity?

I scored a 79.

If you scored between:


Entrepreneurship is almost certainly not for you.

There’s nothing wrong with that. But starting an entrepreneurship venture is the wrong thing to do right now.


You’re kicking the tires of entrepreneurship. Which still means you shouldn’t take the jump yet.

Starting a business and becoming an entrepreneur is an insanely difficult choice. You need more commitment.

Again, nothing wrong with staying at a job. But if you’re not bought in more than this, don’t make the jump.


You are in the beginning stages of becoming a serious, committed entrepreneur.

But you’re still not ready.

More work still needs to be done. At this stage, there are still many books that need to be read, fundamental lessons to be learned, and crucial mindset changes to be had.

If you want to get to the next level:

  • Read 12 books on entrepreneurship in the next 6 weeks.
  • Have informational interviews with 5 new entrepreneurs in your area and ask them about their lives.
  • Be brutally honest in a journal entry about why you’re still hesitant on any of the questions.


You might be ready to start a serious plan to quit your job and start a business.

You might be.

If you’re at this stage, you recognize starting a business and becoming an entrepreneur is one of the hardest things you will ever do in your entire life.

You have a grasp on what it will cost you — money, energy, years of your life. What you must learn. The sacrifices you’ll make that no one else is.

You recognize that “freedom” is actually better than “security.”

But you’re still not all the way bought-in.


It’s time to leave your job.

Right now, you’re spending precious days in a role that will ultimately be simply a stepping stone for your life’s legacy. You need to start preparing to leave, now.

You need an environment that gives you what you desperately crave — freedom. Innovation. Control. Calling the shots, knowing it’s on you if the whole thing goes up in flames.

Most people won’t ever reach this level. That’s OK. This path is not meant for everyone.

But it’s meant for you.

Set a date. That’ll be your last day at the company.

Start planning. Prepare yourself for what you’re about to do (and you better have a plan).

Then make the jump.

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